# US 12,215,082 B1 · (e)-1-(2-(4-substitutedphenyl)-2-oxoethyl)-4-((hydroxyimino)methyl)pyridinium bromides as antitubercular agents

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- Number: US 12,215,082 B1
- Document ID: US12215082B1
- Status: Granted
- Kind: B1
- Application number: 18/743,946
- Filed: 2024-06-14
- Granted: 2025-02-04
- Earliest claimed: 2023-11-01
- Assignees: King Faisal University
- Applicants: King Faisal University
- Inventors: Katharigatta N. Venugopala; Sandeep Chandrashekharappa; Melendran Pillay; Pran Kishore Deb; Rashmi Venugopala
- Web page: https://patentgrep.com/patent/US12215082B1

## CPC

- C07D 213/53: Nitrogen atoms
- A61P 31/06: for tuberculosis
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compounds for treating tuberculosis and, particularly, to anti-tubercular compounds that are (E)-1-(2-(4-substitutedphenyl)-2-oxoethyl)-4-((hydroxyimino)methyl)pyridinium bromides and their use as anti-tubercular agents.

## Claims

### Claim 1

A method of treating tuberculosis in a patient, comprising administering to a patient in need thereof a therapeutically effective amount of a compound having the formula I:
or a pharmaceutically acceptable salt, ester, stereoisomer, or solvate thereof, wherein:
R is selected from the group consisting of hydrogen, halogen, cyano, and nitro.

### Claim 2 (depends on 1)

The method of claim 1, wherein R is selected from the group consisting of hydrogen, NO2, CN, bromine, and fluorine.

### Claim 3 (depends on 1)

The method of claim 1, wherein R is selected from the group consisting of hydrogen, 4-CN, 4-Br, 2-NO2, and 4-F.

### Claim 4 (depends on 1)

The method of claim 1, wherein the compound is selected from the group consisting of:
(E)-4-((Hydroxyimino)methyl)-1-(2-oxo-2-phenylethyl)pyridin-1-ium bromide (3a);
(E)-1-(2-(4-Bromophenyl)-2-oxoethyl)-4-((hydroxyimino)methyl)pyridin-1-ium bromide (3b);
(E)-1-(2-(4-Fluorophenyl)-2-oxoethyl)-4-((hydroxyimino)methyl)pyridin-1-ium bromide (3c);
(E)-1-(2-(4-Cyanophenyl)-2-oxoethyl)-4-((hydroxyimino)methyl)pyridin-1-ium bromide (3d);
(E)-4-((Hydroxyimino)methyl)-1-(2-(2-nitrophenyl)-2-oxoethyl)pyridin-1-ium bromide (3e);
and a pharmaceutically acceptable salt, ester, stereoisomer, or solvate thereof.

### Claim 5 (depends on 1)

The method of claim 1, wherein the tuberculosis comprises multiple drug resistant strains of Mycobacterium tuberculosis.

### Claim 6 (depends on 1)

The method of claim 1, wherein the tuberculosis comprises H37Rv strains of Mycobacterium tuberculosis.

### Claim 7

A method of treating tuberculosis in a patient, comprising administering to a patient in need thereof a therapeutically effective amount of a compound selected from the group consisting of:
(E)-4-((Hydroxyimino)methyl)-1-(2-oxo-2-phenylethyl)pyridin-1-ium bromide (3a);
(E)-1-(2-(4-Bromophenyl)-2-oxoethyl)-4-((hydroxyimino)methyl)pyridin-1-ium bromide (3b);
(E)-1-(2-(4-Fluorophenyl)-2-oxoethyl)-4-((hydroxyimino)methyl)pyridin-1-ium bromide (3c);
(E)-1-(2-(4-Cyanophenyl)-2-oxoethyl)-4-((hydroxyimino)methyl)pyridin-1-ium bromide (3d);
(E)-4-((Hydroxyimino)methyl)-1-(2-(2-nitrophenyl)-2-oxoethyl)pyridin-1-ium bromide (3e);
and a pharmaceutically acceptable salt, ester, stereoisomer, or solvate thereof.

### Claim 8 (depends on 7)

The method of claim 7, wherein the tuberculosis comprises multiple drug resistant strains of Mycobacterium tuberculosis.

### Claim 9 (depends on 7)

The method of claim 7, wherein the tuberculosis comprises H37Rv strains of Mycobacterium tuberculosis.